diff --git a/packages/aws-cdk-lib/package.json b/packages/aws-cdk-lib/package.json
index abc3c2aabaf5e..eb7231dc1fa8a 100644
--- a/packages/aws-cdk-lib/package.json
+++ b/packages/aws-cdk-lib/package.json
@@ -34,7 +34,8 @@
     "eslint": {
       "disable": true
     },
-    "stripDeprecated": true
+    "stripDeprecated": true,
+    "post": ["node ./scripts/verify-readme-import-rewrites.js"]
   },
   "cdk-package": {
     "post": "node ./scripts/verify-stripped-exp.js"
diff --git a/packages/aws-cdk-lib/scripts/verify-readme-import-rewrites.ts b/packages/aws-cdk-lib/scripts/verify-readme-import-rewrites.ts
new file mode 100644
index 0000000000000..a31f721c05dfc
--- /dev/null
+++ b/packages/aws-cdk-lib/scripts/verify-readme-import-rewrites.ts
@@ -0,0 +1,49 @@
+/**
+ * This script verifies the behavior of the `rewriteReadmeImports` method in `ubergen`,
+ * which rewrites '@aws-cdk/...' imports to 'aws-cdk-lib' imports in the package READMEs.
+ * Any verification based on expected state of the live READMEs is going to be somewhat fragile,
+ * but this is the most certain way to be notified if either the tool is broken or the READMEs
+ * have been explicitly changed to no longer reference their import statements.
+ *
+ * The script looks at a few modules with known different import formats and verifies that the
+ * expected rewritten import is present in the generated .jsii manifest.
+ */
+
+import * as path from 'path';
+import * as fs from 'fs-extra';
+
+const jsiiManifestPath = path.resolve(process.cwd(), '.jsii');
+if (!fs.existsSync(jsiiManifestPath)) {
+  throw new Error(`No .jsii manifest file found at: ${jsiiManifestPath}`);
+}
+
+const jsiiManifest = JSON.parse(fs.readFileSync(jsiiManifestPath, { encoding: 'utf-8' }));
+
+// Expected import statements chosen from the individual module READMEs to have a breadth of styles and syntax.
+// If this test fails because one of the below import statements is invalid,
+// please update to have a new, comparable example.
+// This is admittedly a bit fragile; if this test breaks a lot, we should reconsider validation methodology.
+// Count of times this test has been broken by README updates so far (please increment as necessary! :D): 0
+const EXPECTED_SUBMODULE_IMPORTS = {
+  // import * as origins from '@aws-cdk/aws-cloudfront-origins';
+  'aws-cdk-lib.aws_cloudfront_origins': "import { aws_cloudfront_origins as origins } from 'aws-cdk-lib';",
+  // import * as cw from "@aws-cdk/aws-cloudwatch";
+  'aws-cdk-lib.aws_cloudwatch_actions': "import { aws_cloudwatch as cw } from 'aws-cdk-lib';",
+  // import { PhysicalName } from '@aws-cdk/core';
+  'aws-cdk-lib.aws_codepipeline_actions': "import { PhysicalName } from 'aws-cdk-lib';",
+  // import { Rule, Schedule } from '@aws-cdk/aws-events';
+  'aws-cdk-lib.aws_events': "import { Rule, Schedule } from 'aws-cdk-lib/aws-events';",
+  // import * as cdk from '@aws-cdk/core';
+  'aws-cdk-lib.aws_stepfunctions': "import * as cdk from 'aws-cdk-lib';",
+};
+
+Object.entries(EXPECTED_SUBMODULE_IMPORTS).forEach(([submodule, importStatement]) => {
+  const submoduleReadme = jsiiManifest.submodules[submodule]?.readme?.markdown;
+  if (!submoduleReadme) {
+    throw new Error(`jsii manifest for submodule ${submodule} not found`);
+  } else if (!submoduleReadme.includes(importStatement)) {
+    const errorMessage = `Expected to find import statement in ${submodule} README: ${importStatement}\n` +
+      'This may mean the README has changed and this test needs to be updated, or the uberGen rewriteReadmeImports method is broken.';
+    throw new Error(errorMessage);
+  }
+});